Ibuzatrelvir

Ibuzatrelvir
Clinical data
Other names	PF-07817883
Routes of; administration	Oral
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name Methyl N-[(2S)-1-[(2S,4R)-2-[[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]carbamoyl]-4-(trifluoromethyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate;
CAS Number	2755812-39-4;
PubChem CID	163362000;
DrugBank	111;
ChemSpider	128942571;
UNII	KZ2X7QH2VT;
Chemical and physical data
Formula	C21H30F3N5O5
Molar mass	489.496 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)(C)[C@@H](C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@@H](C[C@@H]2CCNC2=O)C#N)C(F)(F)F)NC(=O)OC;
	InChI InChI=1S/C21H30F3N5O5/c1-20(2,3)15(28-19(33)34-4)18(32)29-10-12(21(22,23)24)8-14(29)17(31)27-13(9-25)7-11-5-6-26-16(11)30/h11-15H,5-8,10H2,1-4H3,(H,26,30)(H,27,31)(H,28,33)/t11-,12+,13-,14-,15+/m0/s1; Key:WGNWEPPRWQKSKI-AIEDFZFUSA-N;

Ibuzatrelvir (development code PF-07817883) is an experimental antiviral drug being developed by Pfizer for the treatment of COVID-19.^[1] It is a second-generation improvement over nirmatrelvir which has a similar chemical structure.^[2] One of the disadvantages of nirmatrelvir is that it has low metabolic stability and must be given in combination with ritonavir (as Paxlovid) to limit its metabolic degradation in the body.^[3] Ibuzatrelvir incorporates modifications to the chemical structure of nirmatrelvir that give it enhanced oral bioavailability, so it does not require coadministration with ritonavir.^[3]

References

^ Allerton, Charlotte M. N.; et al. (2024). "A Second-Generation Oral SARS-CoV-2 Main Protease Inhibitor Clinical Candidate for the Treatment of COVID-19". Journal of Medicinal Chemistry. doi:10.1021/acs.jmedchem.3c02469. PMID 38687966.
^ Chen, Pu; Van Oers, Tayla J.; Arutyunova, Elena; Fischer, Conrad; Wang, Chaoxiang; Lamer, Tess; Van Belkum, Marco J.; Young, Howard S.; Vederas, John C.; Lemieux, M. Joanne (2024). "A Structural Comparison of Oral SARS-CoV-2 Drug Candidate Ibuzatrelvir Complexed with the Main Protease (M^pro) of SARS-CoV-2 and MERS-CoV". Jacs Au. doi:10.1021/jacsau.4c00508.
^ ^a ^b Brewitz, Lennart; Schofield, Christopher J. (2024). "Fixing the Achilles Heel of Pfizer's Paxlovid for COVID-19 Treatment". Journal of Medicinal Chemistry. 67 (14): 11656–11661. doi:10.1021/acs.jmedchem.4c01342. PMC 11284777. PMID 38967233.

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[1] Allerton, Charlotte M. N.; et al. (2024). "A Second-Generation Oral SARS-CoV-2 Main Protease Inhibitor Clinical Candidate for the Treatment of COVID-19". Journal of Medicinal Chemistry. doi:10.1021/acs.jmedchem.3c02469. PMID 38687966.

[2] Chen, Pu; Van Oers, Tayla J.; Arutyunova, Elena; Fischer, Conrad; Wang, Chaoxiang; Lamer, Tess; Van Belkum, Marco J.; Young, Howard S.; Vederas, John C.; Lemieux, M. Joanne (2024). "A Structural Comparison of Oral SARS-CoV-2 Drug Candidate Ibuzatrelvir Complexed with the Main Protease (M^pro) of SARS-CoV-2 and MERS-CoV". Jacs Au. doi:10.1021/jacsau.4c00508.

[Brewitz-3] Brewitz, Lennart; Schofield, Christopher J. (2024). "Fixing the Achilles Heel of Pfizer's Paxlovid for COVID-19 Treatment". Journal of Medicinal Chemistry. 67 (14): 11656–11661. doi:10.1021/acs.jmedchem.4c01342. PMC 11284777. PMID 38967233.

[1]

[2]

[3]

Clinical data

Other names	PF-07817883
Routes of administration	Oral
Legal status
Legal status	Investigational
Identifiers
IUPAC name Methyl N-[(2S)-1-[(2S,4R)-2-[[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]carbamoyl]-4-(trifluoromethyl)pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate
CAS Number	2755812-39-4
PubChem CID	163362000
DrugBank	111
ChemSpider	128942571
UNII	KZ2X7QH2VT
Chemical and physical data
Formula	C₂₁H₃₀F₃N₅O₅
Molar mass	489.496 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)(C)[C@@H](C(=O)N1C[C@@H](C[C@H]1C(=O)N[C@@H](C[C@@H]2CCNC2=O)C#N)C(F)(F)F)NC(=O)OC
InChI InChI=1S/C21H30F3N5O5/c1-20(2,3)15(28-19(33)34-4)18(32)29-10-12(21(22,23)24)8-14(29)17(31)27-13(9-25)7-11-5-6-26-16(11)30/h11-15H,5-8,10H2,1-4H3,(H,26,30)(H,27,31)(H,28,33)/t11-,12+,13-,14-,15+/m0/s1 Key:WGNWEPPRWQKSKI-AIEDFZFUSA-N